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Fluorinated surfactants

a technology of fluorinated surfactants and surfactants, applied in the direction of group 5/15 element organic compounds, transportation and packaging, synthetic resin layered products, etc., can solve the problem of more expensive fluorinated materials

Inactive Publication Date: 2007-05-03
THE CHEMOURS CO FC LLC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, fluorinated materials are more expensive.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0068] To a round-bottom flask fitted with a mechanical stirrer and sparged with nitrogen was added C4F9(CH2)4OH (40.1 g). While stirring at 23-24° C., phosphorus pentoxide (8.8 g) was added in portions over a period of 5.5 h. The reaction mixture was then heated to 95° C. for 17 h. After heating, isopropanol (37.8 g) was added over a period of 2 h while the mixture cooled from 95° C. to 65° C. Aqueous ammonia solution (15.9 g, 27%) was then added to the reaction mixture; the temperature rose from 65 to 68° C. during the addition. Deionized water was added next, and the mixture was stirred at 60° C. for 2 h and cooled to room temperature yielding an aqueous solution of the anionic surfactant. The surface tension of the surfactant was measured in deionized water using Test Method 1. Results are listed in Table 2.

examples 2 and 3

[0069] The procedure of Example 1 was repeated replacing the C4F9(CH2)4OH with an equimolar amount of the perfluoroalkylalkanols C4F9(CH2)3OH (Example2), or C6F13(CH2)4OH (Example 3) alcohols to produce the corresponding phosphate surfactants. The surface tension was measured in deionized water using Test Method 1. Results are in Table 2.

example 4

[0074] Perfluoroalkylalkyl alcohol and sodium borohydride (5 mol. %) is charged into a round bottom flask equipped with mechanical stirring and a cold finger condenser (at about −70° C.) and reacted at 85 to 130° C. under nitrogen. The temperature is adjusted to 65 to 100° C., when ethylene oxide is fed over time to the reaction flask, maintaining conditions to avoid the formation of potentially explosive air-ethylene oxide mixtures and uncontrolled reaction of ethylene oxide with solid sodium borohydride. The reaction with ethylene oxide is continued at 65 to 100° C. until the required equivalents of ethylene oxide (typically about 5 to 10 equivalents) are consumed. Vacuum is applied to remove the residual ethylene oxide, and flask is refilled with nitrogen. The product perfluoroalkylalkyl polyethyleneglycol CkF(2k+1)—(CH2)m—O(CH2CH2O)d—H is diluted with water and optionally other co-solvent for further use and surface tension measurements.

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Abstract

A composition of formula I [Rf(CH2)m(O)n]x-A wherein Rf is a straight or branched perfluoroalkyl group having from about 2 to about 20 carbon atoms, or a mixture thereof, m is a positive integer equal to or greater than 3, n is 0 or 1, x is 1 to about 3, A is —P(O)(OR1)y(OM+)3-y-x, —C(O)CH(SO3−M+)CH2C(O)—, —(CH2CH2O)d(CH2CHR2O)eR3, or —SO2B, M+ is an alkali metal ion, NH4+, or NH2+(CH2CH2OH)2, B is N(R2)2 or N(CH2CH3)(CH2CH2OH), R1 is C1 to C3 alkyl, R2 is C1 to C4 alkyl, R3 is H or CH3, y is 0 to about 1, d is 0 to about 16, e is 0 to about 16, provided that (d+e) is from about 3 to about 16 is disclosed.

Description

BACKGROUND OF THE INVENTION [0001] Perfluoroalkylethyl iodides, CkF(2k+1)CH2CH2I, termed “Telomer B iodides”, are prepared by insertion of an ethylene molecule into the perfluoroalkyl iodides of the structure CkF(2k+1)I, “termed Telomer A iodides”. Perfluoroalkylethyl iodides are starting materials for the preparation of fluorinated surfactants and treatment chemicals to provide surfaces with hydrophobic and oleophobic properties. Compounds made from such iodides include, for example, perfluoroalkylethyl(meth)acrylates and various other compounds containing the perfluoroalkylethyl group, and find commercial use in the modification of surface properties. See, for example U.S. Pat. No. 3,721,706. [0002] For surfactants and surface treatment agents containing perfluoroalkyl chains, longer perfluoroalkyl chains contain a higher percentage of fluorine at a given concentration and generally provide better performance. However, fluorinated materials are more expensive. Reducing the fluorin...

Claims

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Application Information

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IPC IPC(8): B32B27/00C07F9/02C07C309/12
CPCC07C309/10C07F9/091C07C309/17C07C67/287Y10T428/31855
Inventor SHTAROV, ALEXANDER BORISOVICHMICHALCZYK, MICHAEL JOSEPHTAYLOR, CHARLES KENNETH
Owner THE CHEMOURS CO FC LLC